Catalyst and preparation method thereof, and preparation method of 1, 1, 4, 4-tetramethoxy-2-butene

A technology of tetramethoxy and catalysts, which is applied in the field of catalysts and preparations for the preparation of 1,1,4,4 tetramethoxy-2-butene, which can solve the problem of low conversion rate of raw materials and low product selectivity and reduced selectivity In order to achieve the effect of improving the conversion rate of process raw materials and product selectivity, improving the subsequent separation of products, and improving the utilization rate of raw materials

Active Publication Date: 2020-12-25
WANHUA CHEM GRP CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The catalyst composition of this method is complicated, and the maximum conversion rate of raw material 2,5-dimethoxy-2,5-dihydrofuran is only about 72%, and a large excess of methanol is used, which is not conducive to industrial scale-up
[0006] Chinese patent CN107952463A discloses a use of Lewis acid or Bronsted acid as an active component, metal nitride or non-metal nitride as a cocatalyst, supported on coconut shell activated carbon as a catalyst, through 2,5-dimethoxy-2, 1,1,4,4-tetraalkoxy-2-butene can be prepared by reacting 5-dihydrofuran with fatty alcohol, and the reaction yield can reach 87%, but there is pentamethoxybutane (PMB) as a by-product , the structural formula Reduced selectivity of the reaction
However, the selectivity of impurity PMB is still high, which is not conducive to product separation
[0008] In summary, it can be seen that the current method for preparing 1,1,4,4-tetramethoxy-2-butene still has problems such as low raw material conversion rate and product selectivity, difficult catalyst recovery, and serious equipment corrosion.

Method used

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  • Catalyst and preparation method thereof, and preparation method of 1, 1, 4, 4-tetramethoxy-2-butene
  • Catalyst and preparation method thereof, and preparation method of 1, 1, 4, 4-tetramethoxy-2-butene
  • Catalyst and preparation method thereof, and preparation method of 1, 1, 4, 4-tetramethoxy-2-butene

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0063] 50 g of multi-walled carbon nanotubes (MWNTs) were weighed and placed in 1000 g of mixed acid with a mass ratio of concentrated sulfuric acid and concentrated nitric acid of 3:1, and ultrasonically dispersed in an ultrasonic cleaner for 1 hour at room temperature. Transfer the ultrasonically dispersed sample into a single-necked flask, react in a constant temperature oil bath at 120°C for 2 hours, transfer it to a beaker after cooling to room temperature, and wash it by high-speed centrifugation (using absolute ethanol / distilled water alternately), and then vacuum-dry dry to obtain acid-modified multi-walled carbon nanotubes (AC-MWNTs).

[0064] Take 45g of acid-modified multi-walled carbon nanotubes (AC-MWNTs) and disperse them in 1800g of thionyl chloride, stir at 70°C for 20h, filter, and wash 3 times with anhydrous tetrahydrofuran to obtain acid chloride-modified multi-walled carbon nanotubes (COCl-MWNTs).

[0065] 40 g of acid chloride-modified multi-walled carbon...

Embodiment 2

[0069] Adjust the amount of carrier, trifluoromethanesulfonic acid, and acetylacetonylbis(ethylene)rhodium to 40g, 6.5g, and 3.84g respectively, and refer to Example 1 for the remaining conditions to prepare catalyst b. According to XPS analysis, its composition is carrier: trifluoromethanesulfonic acid: acetylacetonyl bis(ethylene)rhodium=100.0:15.0:8.0 (mass ratio).

[0070] Adjust the amount of carrier, trifluoromethanesulfonic acid, and acetylacetonyl bis(ethylene)rhodium to 40 g, 21.7 g, and 0.48 g, respectively, and refer to Example 1 for the rest of the conditions to prepare catalyst c. According to XPS analysis, its composition is carrier: trifluoromethanesulfonic acid: acetylacetonyl bis (ethylene) rhodium = 100.0:50.0:1.0 (mass ratio).

Embodiment 3

[0072] Add 96.1g (3mol) methanol, 165.1g (0.8mol) DCC and 130.1g (1mol) 2,5-dimethoxy-2,5-dihydrofuran (DMDF) to the three-necked flask, and use an oil bath to The bottle is heated. When it is heated to an internal temperature of 40°C, weigh 6.5g of catalyst a and add it into the three-necked flask to start the insulation reaction. When the reaction was carried out for 4.0 hours, samples were taken for gas phase analysis. The conversion rate of raw material DMDF was 95.5%, the selectivity of product TMBU was 98.9%, the selectivity of impurity PMB was 0.8%, and the yield of TMBU was 94.4%.

[0073] The catalyst is applied mechanically, and the experimental data are shown in Table 1 below:

[0074] Table 1 Catalyst a application data

[0075]

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Abstract

The invention provides a catalyst and a preparation method thereof, and a preparation method of 1, 1, 4, 4-tetramethoxy-2-butene. The catalyst is prepared from the following components by mass: 100 parts of carrier aromatic ring primary amine modified multi-walled carbon nanotubes; 10-60 parts of an organic strong acid; and 1-10 parts of a rhodium complex or a palladium complex. The method comprises the following steps: under the action of the catalyst, carrying out acetalation reaction on 2, 5-dimethoxy-2, 5-dihydrofuran and methanol by taking a dehydrating agent as an auxiliary agent to prepare 1, 1, 4, 4-tetramethoxy-2-butene; the process has the advantages of high substrate conversion rate, high product selectivity, low environmental pollution and recyclable catalyst, and can overcomethe defects of low reaction yield, serious equipment corrosion and the like in the existing process.

Description

technical field [0001] The invention relates to the field of organic synthesis and catalysts, in particular to a catalyst for preparing 1,1,4,4 tetramethoxy-2-butene and a preparation method thereof. Background technique [0002] 1,1,4,4-Tetramethoxy-2-butene is the key intermediate for the preparation of decatriene dialdehyde (decadecenal for short), and the structural formula of dedecenal is Decenal is an important intermediate for the preparation of carotenoid products, and is of great significance for the synthesis of β-carotene, canthaxanthin, astaxanthin and lycopene. [0003] Many methods have been known for the preparation of 1,1,4,4-tetramethoxy-2-butene for a long time. [0004] U.S. Patent No. 5,338,888A discloses a method of using inorganic or organic strong acid as a catalyst and trimethyl orthoformate as an auxiliary agent to prepare 1,5-dimethoxy-2,5-dihydrofuran and fatty alcohol. 1,4,4-Tetraalkoxy-2-butene, the reaction yield can reach 78%. However, in t...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): B01J31/22B01J31/02C07C43/15C07C43/303C07C41/50
CPCB01J31/2213B01J31/0238B01J31/0232C07C41/50B01J2531/822C07C43/303Y02P20/584
Inventor 张弈宇张涛沈宏强刘英瑞吕英东郭劲资李莉王嘉辉黎源
Owner WANHUA CHEM GRP CO LTD
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